7-methyl-3-methylene-7-octenal acetal compound and methods for producing aldehyde compound and ester compound using the same

Abstract

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4).

The invention claimed is: 
     
       1. A method for producing 3,7-dimethyl-2,7-octadienal of Formula (5): 
       
         
           
           
               
               
           
         
       
       the method comprising steps of:
 hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound of General Formula (1): 
 
       
         
           
           
               
               
           
         
         
           wherein R 1  and R 2 , which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, 
         
       
       in the presence of water under an acidic condition to obtain 7-methyl-3-methylene-7-octenal of Formula (2): 
       
         
           
           
               
               
           
         
       
       and
 isomerizing the 7-methyl-3-methylene-7-octenal (2) in the presence of a base to obtain the 3,7-dimethyl-2,7-octadienal (5). 
 
     
     
       2. A method for producing a 3,7-dimethyl-2,7-octadienyl carboxylate compound of General Formula (7): 
       
         
           
           
               
               
           
         
       
       comprising:
 each step of the method of  claim 1  to produce 3,7-dimethyl-2,7-octadienal of Formula (5); 
 a step of reducing the 3,7-dimethyl-2,7-octadenal (5) with a reducing agent selected from the group consisting of hydrogen, boron compounds, dialkylsilanes, trialkylsilanes, alkylaluminums, dialkylaluminums, metal hydrides, and complex hydrides and alkoxy or alkyl derivatives thereof, to obtain 3,7-dimethyl-2,7-octadienol of Formula (6): 
 
       
         
           
           
               
               
           
         
       
       and
 esterifying the 3,7-dimethyl-2,7-octadienol (6) through a reaction with an acylating agent, a reaction with a carboxylic acid, a transesterification, or a method in which the 3,7-dimethyl-2,7-octadienol (6) is converted into an alkylating agent and then the alkylating agent is reacted with a carboxylic acid, to obtain the 3,7-dimethyl-2,7-octadienyl carboxylate compound (7).